Anna Maria Vacation Rentals
Our collection of homes in the City of Anna Maria offers a quieter, more residential side of island living, known for its natural beauty, charming streets, and close proximity to Bean Point and the Gulf’s most pristine beaches. This area captures the essence of old Florida, where mornings are slow, sunsets are uninterrupted, and everything feels intentionally unspoiled.
From thoughtfully designed beach homes to private coastal retreats, each stay is curated for comfort, style, and a seamless connection to the island’s most sought-after experiences.
19 properties available
Welcome to Anna Maria Aloha!On Anna Maria Island (Anna Maria, Florida)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience Anna Maria Aloha — a tranquil island cottage made for rest, renewal, and connection.Nestled on the peaceful North End of Anna Maria Island, just 500 feet f
Welcome to Tern Key!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceTern Key is a home that feels both artful and effortless — where every line, light, and texture come together in perfect harmony. The moment you step inside, the canal vi
Welcome to Sunset at 714!On Anna Maria Island (Anna Maria, FL)Managed locally by Once Upon A Beach Vacation Rentals & Property ManagementThe SpaceWhere island sunsets, beach days, and family memories come together.Tucked away on the highly desirable north end of Anna Maria Island, Sunset at 714 places you just a short stroll from the sugar-whit
Welcome to The Palm at Bean Point!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation RentalsWhere modern luxury meets laid-back island living, just moments from Bean Point.Tucked away in one of Anna Maria Island's most beloved neighborhoods, this beautifully renovated coastal retreat offers everything you need for a rela
Welcome to Point's Hideaway!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Please note: The home is next to a construction site. There is no set construction schedule, and activity may occur during your stay.The SpaceEvery corner of Point’s H
Welcome to The Cottage on Pine!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceStep inside The Cottage on Pine and feel the ease of island life take hold. Gentle natural light, soft coastal hues, and thoughtfully curated details create an atmos
Welcome to Coconut Lagoon!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceStep into Coconut Lagoon, where generations of island charm meet easy, family-focused living. Nestled along the beloved Magnolia Avenue—lined with palms, bike
Welcome to Hangin’ on Hammock!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Tucked along a quiet stretch on the north end of Anna Maria Island, this home blends easy island living with space to gather, unwind, and enjoy the water. Fresh paint, u
Welcome to La Buena Vida!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.The SpaceMornings begin with sunlight dancing across the canal and coffee enjoyed on the screened porch. Days unfold between the pool, the dock, and the nearby beach—each mom
Welcome to Casa Mariposa!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.Experience Casa Mariposa where the rhythm of island life slows, and beauty unfolds in every detail. Just one street north of Pine Avenue and four houses from the beach, this elegan
Welcome to Sol Mate!On Anna Maria Island (Anna Maria, FL)Managed locally by Once Upon A Beach Vacation Rentals & Property ManagementThe SpaceYour island escape designed for families and friends to slow down, reconnect, and soak in the simple joys of island life. Nestled near Anna Maria’s most scenic shoreline and moments from Pine Avenue,
Welcome to Happy Ours!On Anna Maria Island (Anna Maria, FL)Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.JUST RELAUNCHED AS A RENTAL and UNDER NEW MANAGEMENT! Experience Happy Ours — a rare direct beachfront retreat tucked along Magnolia Avenue on Anna
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